After an auspicious film debut as a helpful geek in the 1999 sci-fi comedy Galaxy Quest, Long came to prominence as an awkward adolescent on the dramedy Ed. On the big screen, he popped up in teen-oriented fare (the Jeepers Creepers horror flicks) and played boyfriend to two pop queens: Britney Spears in Crossroads and Lindsay Lohan in Herbie: Fully Loaded. But he also cracked up older audiences in Dodgeball: A True Underdog Story, which prompted costar Vince Vaughn to cast the up-and-comer in 2006's The Break-Up. Long has also tackled blockbusters, like 2007's Live Free or Die Hard, and mature romantic comedy, including 2009's He's Just Not That Into You, in which he costarred with on-again, off-again love interest Drew Barrymore.